Anticancer (hexacarbonyldicobalt)propargyl aryl ethers: Synthesis, antiproliferative activity, apoptosis induction, and effect on cellular oxidative stress

Schimler, Sydonie D.; Hall, D.; Debbert, Stefan L.

doi:10.1016/j.jinorgbio.2012.10.014

Cited by 26 publications

(26 citation statements)

References 50 publications

(68 reference statements)

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“…It may be possible that HBLi complexes exert their biological activities by direct interaction with the DNA. Research in this area indicated that organometallic complexes, particularly transition metal ion group, interact with DNA noncovalently producing changes in the structure of the DNA, thereby interfering with cell cycle and induce apoptosis [7,[17][18][19][20][21][22]. HBLi complexes induceing apoptosis, which was detected by annexin V labelling and confirmed morphologically by SEM, in concentration-and structure-dependent manners.…”

Section: Discussionmentioning

confidence: 99%

The Effect of Hydroxybenzoate Lithium Complexes in Inducing Apoptosis in HT-1080 Human Fibrosarcoma Cells

Mahdi

Al-Hazzaa

et al. 2013

Journal of Cancer Research

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There has been a growing interest in the beneficial effects of simple phenolic acids and their ability to exhibit various biological activities. The aim of this study was to assess in vitro biological activities of 2-, 3-, and 4-hydroxybenzoate lithium (HBLi) complexes on HT-1080 human fibrosarcoma cells by methods of using a metabolic activity assay, immunochemical and morphological techniques. Results showed that HBLi complexes exert their cytotoxic activities in a concentration-and chemical structuredependent manner in the following order: 4-HBLi > 3-HBLi > 2-HBLi. Flow cytometry displayed evidence of apoptosis induced by 3-HBLi (21.8%) and 4-HBLi (33.2%). These results were verified by SEM, which revealed the formation of apoptotic bodies. In addition, these 3-HBLi and 4-HBLi caused an increase in HT-1080 cell cycle arrest in G0/G1 phase when compared to the controls (25% and 30.6%, resp.) when cells were treated with 6 mM for 24 hours. Immunochemical studies related to the molecular mechanism of apoptosis indicated that HBLi complexes downregulated the expression of Bcl-2 and upregulated Bax, p53, and caspases-3 in a concentration-dependent manner. HBLi complexes lowered Bcl-2/Bax ratios and induced the expression of p53 and caspase-3. These results suggest that HBLi complexes may exert their apoptotic effects through mitochondrial-mediated, caspasedependent, apoptotic mechanisms.

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Section: Discussionmentioning

confidence: 99%

The Effect of Hydroxybenzoate Lithium Complexes in Inducing Apoptosis in HT-1080 Human Fibrosarcoma Cells

Mahdi

Al-Hazzaa

et al. 2013

Journal of Cancer Research

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“…Indeed, the attachment was more efficient than for cisplatin. Cell cycle analysis of MDA-MB 231 cells after incubation with 44 (Figure 1.15) revealed an increased amount of cells in the S phase, and less in the G 2 /M phase [115]. This suggests that the interaction with DNA results from the cobalt-alkyne moiety.…”

Section: Novel Mechanisms Of Enzyme Inhibition With Organometallic Comentioning

confidence: 99%

Organometallic Complexes as Enzyme Inhibitors: A Conceptual Overview

Anstaett

Gasser

2014

Bioorganometallic Chemistry

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“…Even though there have been reports of cytotoxic activity associated to some hexacarbonyl dicobalt complexes [45,46], the compounds described in this study have not yet been submitted to biological evaluation. However, decobaltation of these derivatives was straightforward and several methods were used to that end: tetrabutylamonnium fluoride (TBAF) in THF [47], trimethylamine N-oxide (TMANO) [48], and iodine/THF [49].…”

Section: Unmasking Of Alkynes From Hexacarbonyl Dicobalt Derivativesmentioning

confidence: 99%

Ferrier–Nicholas pyranosidic cations: application to diversity-oriented synthesis

López

Lobo

Miranda

et al. 2014

Pure and Applied Chemistry

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Pyranosidic allylic (Ferrier) cations that share dicobalt hexacarbonyl propargyl (Nicholas) stabilization at C-1, can be easily generated by treatment of hexacarbonyldicobalt alkynyl glycals with BF 3 ·OEt 2 , and display a remarkable reactivity leading to a variety of products. The substituent at O-6 in these glycals plays a pivotal role in directing the outcome of the transformations. Accordingly, 6-O-benzyl or 6-O-allyl groups cause a series of transformations resulting in the stereoselective formation of oxepanes through a process that involves an initial hydride transfer step from the allyl or benzyl substituent to the Ferrier-Nicholas cation. On the contrary, 6-OH derivatives undergo an overall ring contraction to branched tetrahydrofuran derivatives. 6-O-Silyl derivatives, in the presence of heteroaryl nucleophiles, were transformed into C-3 branched bis-C-Cglycosides, containing two of such molecules.

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Anticancer (hexacarbonyldicobalt)propargyl aryl ethers: Synthesis, antiproliferative activity, apoptosis induction, and effect on cellular oxidative stress

Cited by 26 publications

References 50 publications

The Effect of Hydroxybenzoate Lithium Complexes in Inducing Apoptosis in HT-1080 Human Fibrosarcoma Cells

The Effect of Hydroxybenzoate Lithium Complexes in Inducing Apoptosis in HT-1080 Human Fibrosarcoma Cells

Organometallic Complexes as Enzyme Inhibitors: A Conceptual Overview

Ferrier–Nicholas pyranosidic cations: application to diversity-oriented synthesis

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